EP0316795A2 - Adoucissant textile liquide - Google Patents

Adoucissant textile liquide Download PDF

Info

Publication number: EP0316795A2
Authority: EP; European Patent Office
Prior art keywords: radicals; straight; amines; carbon atoms; chain
Prior art date: 1987-11-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP88118812A

Other languages

German (de)

English (en)

Other versions

EP0316795A3 (fr

Inventor

Horst Dr. Rutzen

Eric Dr. Sung

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Henkel AG and Co KGaA

Original Assignee

Henkel AG and Co KGaA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-11-19

Filing date

1988-11-11

Publication date

1989-05-24

1988-11-11 Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA

1989-05-24 Publication of EP0316795A2 publication Critical patent/EP0316795A2/fr

1990-01-17 Publication of EP0316795A3 publication Critical patent/EP0316795A3/fr

Status Withdrawn legal-status Critical Current

Links

239000004753 textile Substances 0.000 title abstract description 12
239000007788 liquid Substances 0.000 title 1
150000001412 amines Chemical class 0.000 claims abstract description 74
239000002979 fabric softener Substances 0.000 claims abstract description 63
150000003460 sulfonic acids Chemical class 0.000 claims abstract description 20
150000003009 phosphonic acids Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 9
-1 alkenyl radical Chemical class 0.000 claims description 111
125000004432 carbon atom Chemical group C* 0.000 claims description 53
150000001875 compounds Chemical class 0.000 claims description 29
150000003254 radicals Chemical class 0.000 claims description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 14
238000005956 quaternization reaction Methods 0.000 claims description 14
150000003868 ammonium compounds Chemical class 0.000 claims description 13
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
235000019387 fatty acid methyl ester Nutrition 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
125000001033 ether group Chemical group 0.000 claims description 3
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 2
229940073608 benzyl chloride Drugs 0.000 claims description 2
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 2
229960003750 ethyl chloride Drugs 0.000 claims description 2
239000004480 active ingredient Substances 0.000 abstract description 6
238000005406 washing Methods 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 21
239000000203 mixture Substances 0.000 description 21
239000004744 fabric Substances 0.000 description 9
235000014113 dietary fatty acids Nutrition 0.000 description 8
239000000194 fatty acid Substances 0.000 description 8
229930195729 fatty acid Natural products 0.000 description 8
239000003921 oil Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000003925 fat Substances 0.000 description 6
235000019197 fats Nutrition 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
239000004902 Softening Agent Substances 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000000470 constituent Substances 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000005809 transesterification reaction Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
239000003093 cationic surfactant Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
230000001953 sensory effect Effects 0.000 description 3
235000019832 sodium triphosphate Nutrition 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical group N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000003599 detergent Substances 0.000 description 2
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003760 tallow Substances 0.000 description 2
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 1
FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
229910018828 PO3H2 Inorganic materials 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
235000019865 palm kernel oil Nutrition 0.000 description 1
239000003346 palm kernel oil Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid

Definitions

the invention relates to fabric softeners that can be used for the treatment of textiles after washing.
Fabric softener is usually understood to mean ready-to-use or ready-to-use agents containing one or more active ingredients, which are used in the detergent and detergent sector and are used to give textiles a soft feel. Such agents usually contain one or more cationic surfactants which are able to make textiles treated with them soft and easy to grip.
water-insoluble quaternary ammonium compounds have been proposed as cationic surfactants, in which the ammonium nitrogen atom, in order to ensure sufficient softener qualities of the fabric softener, has at least two long-chain aliphatic radicals with 16 to 18 carbon atoms or at least one excessively long radical, for example with carbon atom numbers in the range from 32 to 36, the long or excessively long residues can be interrupted by ether, ester or amido groups.
Quaternary ammonium compounds of this type were specially produced for the manufacture of fabric softeners in large quantities and mostly in a complex manner.
the present invention has set itself the task of avoiding the disadvantages known from the prior art, in particular the use of fabric softener constituents produced by complex synthesis, and of providing fabric softener, the active ingredients of which by simple chemical synthesis from inexpensive raw materials or from a large scale Synthesizable intermediates can be produced. It was surprisingly found that fabric softeners with a good softening effect (softening effect) can be obtained by simply mixing certain sulfonic acids and / or phosphonic acids and fatty amines or corresponding quaternary compounds of the fatty amines, which are inexpensively accessible on a large scale by simple oleochemical syntheses from natural raw materials .
the fabric softeners according to the invention can therefore contain a large number of compounds of the general formulas (I) and (II) as amine components.
one or more ammonium compounds are also suitable as "amine component", which are quaternized from amines of the general formulas (I) and / or (II) are derived.
straight-chain alkyl radicals come independently from the group as meaning for R 1 and R 2 Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl and eicosyl as well as the branched homologs of the aforementioned which can be used with the same advantage in principle Alkyl residues in question.
alkyl groups mentioned are interrupted by ether groups. This means nothing other than that oxygen atoms, which originate from alkoxylation reactions of corresponding alkyl radicals or their derivatives, can be inserted into - in particular longer - alkyl radicals.
R 1 in the above general formula (II) is a radical of the formula CH3- (CH2) n -CO-NH- (CH2) 3- in which the index can take n values in the range from 8 to 18.
Such fatty acid amidoalkyl radicals are then bound directly to the amino nitrogen atom or - in the case of the ammonium compounds derived from such amines by quaternization - to the ammonium nitrogen atom.
R2 can also have further meanings.
the amines which can be used in fabric softeners can also represent a hydroxyl group or a group of the formula (III) in the R5 is hydrogen or an alkyl radical from the group methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, the pentyl radicals which are homologous to n-pentyl and n-hexyl and the branched-chain hexyl radicals isomeric to n-hexyl.
R3 and R4 in the amines which can be used in the fabric softeners according to the invention, in addition to hydrogen, can also be straight-chain or branched alkyl radicals having 1 to 6 carbon atoms.
R3 and R4 in the amines which can be used in the fabric softeners according to the invention, in addition to hydrogen can also be straight-chain or branched alkyl radicals having 1 to 6 carbon atoms.
residues methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, n-hexyl and the branched pentyl and isomers which are isomeric to the straight-chain pentyl and hexyl radicals Hexyl residues in question.
R3 and R4 in the general formulas (I) and (II) also represent hydroxyalkyl radicals in which the alkyl groups are always straight-chain and come from the group of the radicals methyl, ethyl, propyl, butyl, pentyl and hexyl.
the indices p and q can stand for numbers in the range from 0 to 22, the sum (p + q) always being in the range from 0 to 22. It is possible for p and q to assume any possible number in the range mentioned. This can also include fractional numbers, since - as will be explained later - compound mixtures are used in which there are different numbers of -CH2 groups in the molecule and the indices p and q only indicate the average numerical values; Due to the occurrence of compound mixtures of different proportions in a mixture, even fractional numbers as indices for p and q are possible.
the usable amines of the general formula (I) can be divided into several groups.
one or more compounds of the general formula (I) are preferably used as the amine component, in which R1 and R2 are hydrogen, R3 and R4 independently of one another for straight-chain or branched alkyl radicals with 1 to 6 carbon atoms or hydroxyalkyl radicals with 1 to 6 carbon atoms in the alkyl radical.
the fabric softeners contain one or more amines of the general formula (I) in which R1 is hydrogen or straight-chain or branched alkyl radicals having 1 to 20 C atoms and R2 is a hydroxyl group or a group of the formula (III) in which R5 is hydrogen or a straight-chain or branched C1-C6 alkyl radical.
amines are formed in accordance with the reaction equation (2) below from epoxidized fatty acids, fatty acid esters or fatty alcohols, which are cheaply accessible in large quantities from animal or vegetable fats or oils, i.e. from natural sources, and not only as individual substances, but also as natural ones Sources resulting mixtures can be used.
Such mixtures include not only mixtures of compounds of different chain lengths as they occur in natural fats and oils - as homologues of otherwise identical structure - but also mixtures of compounds which carry epoxy groups at different positions in the molecular chain and thus also in lead in different ways through the reaction with the corresponding amines to give mixtures of ring-opening products of the general formula (I).
the product mixtures of the general formula (I) resulting from reaction equation (2) are suitable as amine component of the fabric softener according to the invention.
the fabric softeners contain one or more amines of the general formula (I) in which R1 is a straight-chain or branched alkyl radical having 1 to 20 C atoms and R2 is a hydroxyl group or a group of the formula (III) in which R5 has the meanings given above, and R3 and R4 independently of one another represent straight-chain or branched alkyl radicals having 1 to 6 C atoms or hydroxyalkyl radicals having 1 to 6 C atoms in the straight-chain alkyl radical.
R1 is a straight-chain or branched alkyl radical having 1 to 20 C atoms
R2 is a hydroxyl group or a group of the formula (III) in which R5 has the meanings given above
R3 and R4 independently of one another represent straight-chain or branched alkyl radicals having 1 to 6 C atoms or hydroxyalkyl radicals having 1 to 6 C atoms in the straight-chain alkyl radical.
R3 and R4 in the general formula (I) of the amine or amines used from the group of straight-chain alkyl radicals with 1 to select 3 carbon atoms and the hydroxyalkyl radicals with 1 to 3 carbon atoms in the straight-chain alkyl radical, in which case p 8 to 18 and q is 0.
R1R3R4N R1 can be hydrogen, straight-chain or branched alkyl radicals having 1 to 20 C atoms, as already mentioned above, and R3 and R4, which can be the same or different, can independently of one another be hydrogen, straight-chain or branched Alkyl residues with 1 to 6 carbon atoms or hydroxyalkyl radicals with 1 to 6 carbon atoms in the straight-chain alkyl radical.
the radical R 1 in the general formula (II) usually has a number of carbon atoms in the range from 12 to 20, preferably from 14 to 18.
Amines with chain lengths in this preferred range can be conveniently synthesized from natural fats and oils by methods known per se. Because of the synthesis methods usually used, mixtures of amines of different chain lengths are usually obtained on an industrial scale and can be readily contained in the fabric softening agents according to the invention as an amine component. However, it is also possible to synthesize individual compounds and to provide them as an amine component of the fabric softener. From the group of the amines of the general formula (II) mentioned, laurylamine, cetylamine, lauryldimethylamine and cetyldimethylamine have proven particularly useful in practice.
amine component together with or instead of the abovementioned amines of the general formulas (I) and (II), one or more, by quaternization from amines of the general formulas (I ) and (II) to use derived ammonium compounds.
ammonium compounds can be used both as individual components and as mixtures of several ammonium compounds. It is irrelevant in which molar ratio they are mixed with the amines of the general formulas (I) and (II) mentioned above or in which molar ratios they are contained among one another in the fabric softeners according to the invention.
ammonium compounds are advantageously used in addition to or instead of the amines of the general formulas (I) and / or (II) are derived by quaternization of the abovementioned amines of the general formulas (I) and (II) with a compound of the general formula (IV) (R8) m X (IV) in the stands.
the alkyl radicals R8 in the quaternizing reagent are the groups methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl or t-butyl from the group of the alkyl radicals or the benzyl or phenethyl radicals from the group of the phenalkyl radicals Question.
X can represent the acid residue of a large number of organic and / or inorganic acids; Usually, the residues chloride, bromide, methosulfate, ethosulfate, toluenesulfonate are to be considered as acid residue X.
ammonium compounds those which are derived from the compounds of the general formulas (I) and / or (II) by quaternization with a quaternizing reagent from the group consisting of methyl chloride, ethyl chloride, benzyl chloride and dimethyl sulfate are used with particular advantage.
reaction of the quaternization of the amines of the general formulas (I) and / or (II) with the quaternization reagents mentioned is generally known as such. It is also used to produce the ammonium compounds which can also be used according to the invention in the manner known from the prior art and way performed. This consists in reacting the respective amines in the presence or in the absence of a solvent at elevated temperature with the desired quaternizing reagent.
the quaternization in a manner which is likewise known from the prior art by reacting the respective amine with an alkylene oxide, preferably with ethylene oxide, in the presence of an acid and thereby obtaining quaternization products which carry a hydroxyalkyl group instead of the hydrogen atom in the amine, the number of carbon atoms in the alkyl chain corresponding to the number of carbon atoms in the alkylene oxide used for the reaction and the statistical number of alkoxy groups by the molar ratio of alkylene oxide: amine set during the reaction is determined.
the quaternary ammonium compounds formed in this way contain as anion X the acid residue of the acid used in the reaction.
the radical X stands for example for a chloride, sulfate, acetate, lactate, phosphate or benzoate radical.
the fabric softeners according to the invention which contain one or more amines of the general formula (I) or (II) and / or quaternary ammonium compounds derived therefrom as the amine component, have, as a further essential component, one or more sulfonic acids of the general formulas (V), (VI) , (VII) and (VIII) on, and / or one or more phosphonic acids of the general formulas (IX), (X), (XI) and (XII) in which R6 for straight-chain or branched alkyl or alkenyl radicals with 1 to 18 carbon atoms and R7 stand for straight-chain or branched alkyl radicals with 1 to 6 carbon atoms.
Suitable sulfonic acids are therefore individual compounds or mixtures of those compounds of the general formula (V) which arise from fatty acid alkyl esters of the general formula (XIII) and SO3 according to the following reaction equation (3) by processes known per se from the prior art:
fatty acids esters (XIII) or mixtures of such esters derived from natural fats and / or oils and converted into compounds of the formula (XIII) by transesterification in a manner known from the prior art are used in practice as starting materials for this reaction.
fatty acids or mixtures of fatty acids derived from fats or oils of natural origin and with an alcohol of the general formula can also be used R7OH were converted into a fatty acid ester (XIII) or a mixture of several such esters.
the radicals R6 in such sulfonic acids can mean straight-chain alkyl radicals from the group methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and Have octadecyl.
straight-chain alkyl radicals it is also conceivable to use those which have a corresponding number of carbon atoms and are branched at any one or more positions in the molecule.
straight-chain alkyl radicals R6 are preferred.
R7 radicals represent alkyl radicals having 1 to 6 carbon atoms. These can therefore be radicals from the group consisting of methyl, ethyl, propyl, butyl, pentyl and hexyl, with straight-chain and branched radicals from this group also being conceivable here.
the compounds of the above general formula (V) are usually obtained in practice by the carboxylic acid esters of the general formula (XIII), which can originate directly from natural sources or by transesterification, hydrogenation hardening or the like known from the prior art Reactions were made from such, implemented with SO3. This also takes place according to methods known from the prior art. For example, such reactions take place at temperatures in the range of 60 to 90 ° C and SO3 partial pressures in the range of 0.03 to 0.1 bar in the presence of a suitable organic solvent or in the absence of solvents. Reactions of mixtures (XIII) accordingly also lead to mixtures of the compounds of the general formula (V), which can be separated if desired, but can usually be used as such as an acid component for the fabric softener according to the invention.
the fabric softeners according to the invention contain one or more sulfonic acids of the general formula (VI) instead of or in addition to the compounds of the general formula (V).
the radical R6 has the meaning already given for the sulfonic acids of the general formula (V).
the alkyl radicals or alkenyl radicals R6 can be at any point on the aromatic ring.
particularly preferred embodiments of the invention contain one or more compounds in the fabric softening agents in which R6 for straight-chain alkyl radicals having 12 to 16 carbon atoms and / or R7 represent methyl or ethyl.
Sulfonic acids or sulfonic acid mixtures of compounds from the group of hydropalm nucleic fatty acid methyl ester sulfonic acid, hydrotalg fatty acid methyl ester sulfonic acid, dodecylbenzenesulfonic acid and p-toluenesulfonic acid have proven particularly useful.
“Hydropalm kernel fatty acid methyl ester sulfonic acid” is understood to mean those compounds which can be obtained from palm kernel oils by transesterification with methanol and hydrogenation of the unsaturated alkyl radicals and subsequent reaction with SO 3 in accordance with the above reaction equation.
“Hydrotalg fatty acid methyl ester sulfonic acid” is understood to mean those compounds which are obtained from tallow by transesterification and hydrogenation of the unsaturated constituents and subsequent reaction with SO3.
the fabric softeners contain one or more acids of the general formulas (VII) and (VIII) instead of or in addition to the compounds of the general formulas (V) and / or (VI).
radicals R6 and R7 can have the meanings already defined above in connection with the sulfonic acids (V) and (VI). In this context, preference is also given to those alkyl radicals R6 which have 12 to 16 C atoms and / or R7 which are methyl or ethyl.
one or more phosphonic acids of the general formula can preferably be present in the fabric softeners according to the invention.
R6 has the meanings which have already been mentioned above in connection with the general formulas (V) and (VI).
Compounds (IX) in which R6 represents straight-chain alkyl radicals having 12 to 16 carbon atoms are particularly preferred.
Tetradecyl-1-phosphonic acid has proven particularly useful as a phosphonic acid component in the fabric softeners according to the invention.
the fabric softeners according to the invention can also contain other phosphonic acids of the general formulas (X), (XI) and (XII) contain.
the R6 radicals also represent straight-chain or branched alkyl radicals or alkenyl radicals having 1 to 18 C atoms
the R7 radicals represent straight-chain or branched alkyl radicals having 1 to 6 C atoms, whereby - as already mentioned for the above Sulfonic acids defined - straight-chain alkyl radicals having 12 to 16 carbon atoms are preferred for the radicals R6, while methyl radicals or ethyl radicals are preferred for the radicals R7.
the fabric softeners according to the invention usually contain the components mentioned, i.e. Amines of the general formulas (I) and / or (II) and / or quaternary ammonium compounds derived therefrom by quaternization on the one hand and sulfonic acids of the general formulas (V) to (VIII) and / or phosphonic acids of the general formulas (IX) to (XII) on the other hand in certain quantities.
the amount of amine component is usually in the range from 10 to 90 mol%, while the amount of sulfonic acids and / or phosphonic acids is usually in the range from 90 to 10 mol%.
the fabric softener according to the invention also contains water as a further component. This is present in the agents in an amount which adds up to 100% by weight with the amounts of the amine component and the sulfonic acid and / or phosphonic acid component and with the other constituents which may be present.
the fabric softeners may also contain further substances conventionally used in such compositions. These can be, for example, fragrances, coloring substances, solvents, preservatives and viscosity regulators. Such substances are usually present in the fabric softener in amounts of 0 to 50% by weight, based on the total weight of the fabric softener. However, their presence or absence does not affect the fabric softening result.
the amine component, sulfonic acid or phosphonic acid component and, if appropriate, further fabric softening agents according to the invention containing other constituents are packaged on an aqueous basis.
the amounts of water are adjusted so that easy-to-handle, low-viscosity fabric softeners are produced, which in this form can be easily introduced into the post-wash liquor.
the amounts of water in the ready-made fabric softeners according to the invention are usually in the range from about 98 to about 50% by weight.
the fabric softeners according to the invention are produced by processes known per se from the prior art. This is essentially due to the fact that the individual components are mixed with one another in commercially available mixers. If desired, this is done using a solvent and / or at a slightly elevated temperature.
the solvents that can be used for the production are expediently selected so that they can remain in the ready-made fabric softener. Examples of suitable solvents are ethanol, n-propanol, i-propanol, ethylene glycol, propylene glycol, diglycols and polyglycols. Suitable concentrations largely depend on the specific case, ie the miscibility of Amine component and carboxylic acid component dependent on water and can be selected within wide limits. An important criterion for the selection of the type and the amount of the solvent used in the production is the compatibility with water.
the fabric softeners according to the invention obtained in this way are essentially soluble or finely dispersible in the aqueous phase and therefore have a particularly high storage stability.
they When used in liquors, they are usually used in concentrations of 0.1 to 0.6 g / l, based on the amine and sulfonic acid or phosphonic acid components, and show the desired softening result in this concentration range. They give the textiles washed with them a good fluffiness and a soft feel, which test persons found to be extremely pleasant.
the essential components used for the preparation of the agents according to the invention are easily accessible on an industrial scale from inexpensive, partly natural sources. Separating or cleaning operations of the individual components are not required for the production of the agents according to the invention.
Fabric softeners according to the invention were produced using the components shown in Table 1 below.
the acid component and the amine component were reacted with one another in a molar ratio of 1: 1 while heating on a steam bath to approx. 80 ° C. and stirring occasionally.
Tetradecyl-1-phosphonic acid and dimethylhexadecylamine were reacted in a molar ratio of 1: 1 at about 80 ° C. in a manner corresponding to Examples 1 to 6 above.
the mixtures obtained according to Examples 1 to 7 were dispersed in water.
the active ingredient concentration of the fabric softener according to the invention was 0.3 g / l water.
the terry samples were tested for their softness in comparison to the hard starting material by people who were skilled in the evaluation of the softness of textiles. The test was based on an evaluation scale in which the values can fluctuate between 0 (very hard grip) and 6 (very soft grip).
the treated textiles have a very good fluffiness or great softness after drying.
the absorbency of the treated textiles was not affected after drying compared to the untreated state.

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Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Organic Chemistry (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

EP88118812A 1987-11-19 1988-11-11 Adoucissant textile liquide Withdrawn EP0316795A3 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3739143		1987-11-19
DE19873739143 DE3739143A1 (de)	1987-11-19	1987-11-19	Waessriges weichspuelmittel fuer die behandlung von textilien

Publications (2)

Publication Number	Publication Date
EP0316795A2 true EP0316795A2 (fr)	1989-05-24
EP0316795A3 EP0316795A3 (fr)	1990-01-17

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ID=6340753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP88118812A Withdrawn EP0316795A3 (fr)	1987-11-19	1988-11-11	Adoucissant textile liquide

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US (1)	US4913829A (fr)
EP (1)	EP0316795A3 (fr)
JP (1)	JPH01162873A (fr)
DE (1)	DE3739143A1 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
JPH0759792B2 (ja) *	1990-08-22	1995-06-28	花王株式会社	柔軟仕上剤
US5282983A (en) *	1990-08-22	1994-02-01	Kao Corporation	Fabric softener composition and ammonium salt
DE4325783A1 (de) *	1993-07-31	1995-02-02	Hoechst Ag	Verfahren zum Modifizieren und Färben von modifizierten Fasermaterialien
DE69616092T2 (de) *	1996-01-19	2002-03-14	Unilever N.V., Rotterdam	Nicht-kationische systeme für gewebetrocknerblätter
US6001137A (en) *	1998-02-27	1999-12-14	Encad, Inc.	Ink jet printed textiles
US6063369A (en) *	1998-03-16	2000-05-16	Alterna, Inc.	Quaternized hemp seed oil
US7207766B2 (en) *	2003-10-20	2007-04-24	Applied Materials, Inc.	Load lock chamber for large area substrate processing system
RU2748253C2 (ru) *	2016-12-26	2021-05-21	Као Корпорейшн	Способ обработки текстильного продукта

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4213867A (en) *	1978-12-29	1980-07-22	Domtar Inc.	Fabric conditioning compositions
DE3150178A1 (de) *	1981-12-18	1983-06-30	Hoechst Ag, 6230 Frankfurt	"konzentrierte waescheweichspuelmittel"
EP0121949A1 (fr) *	1983-02-15	1984-10-17	THE PROCTER & GAMBLE COMPANY	Mélange de détergent anionique/cationique avec une structure irrégulière
DE3638918A1 (de) *	1986-11-14	1988-05-26	Henkel Kgaa	Quartaere ammoniumverbindungen, deren herstellung und verwendung als textilnachbehandlungsmittel
DE3708132A1 (de) *	1987-03-13	1988-09-22	Henkel Kgaa	Waessriges weichspuelmittel fuer die behandlung von textilien

1987
- 1987-11-19 DE DE19873739143 patent/DE3739143A1/de not_active Withdrawn
1988
- 1988-11-11 EP EP88118812A patent/EP0316795A3/fr not_active Withdrawn
- 1988-11-16 US US07/272,171 patent/US4913829A/en not_active Expired - Fee Related
- 1988-11-19 JP JP63293441A patent/JPH01162873A/ja active Pending

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EP0316795A3 (fr)	1990-01-17
US4913829A (en)	1990-04-03
JPH01162873A (ja)	1989-06-27

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Publication	Publication Date	Title
DE2728841C2 (fr)	1988-09-29
EP0789742B1 (fr)	1998-12-16	Agent de post-traitement pour le linge
EP2563889B1 (fr)	2017-03-15	Composition d'adoucissant pour textile
DE3884054T2 (de)	1994-02-03	Quaternäre Monoesterammoniumverbindungen als Faser- und Gewebebehandlungsmittel.
EP0281975A2 (fr)	1988-09-14	Adoucissant aqueux pour le traitement de matières textiles
EP0284036A2 (fr)	1988-09-28	Procédé pour la fabrication d'esteramines quaternaires et leur utilisation
DE4224714A1 (de)	1994-02-03	Schäumende Detergensgemische
DE4215478A1 (de)	1993-11-18	Lactobionsäureamidzusammensetzungen und deren Verwenndung
DE3638918A1 (de)	1988-05-26	Quartaere ammoniumverbindungen, deren herstellung und verwendung als textilnachbehandlungsmittel
DE3818061A1 (de)	1989-12-07	Fluessiges, waessriges waeschenachbehandlungsmittel
EP0316795A2 (fr)	1989-05-24	Adoucissant textile liquide
DE2811152A1 (de)	1978-10-12	Konzentriertes waescheweichspuelmittel
DE3730444A1 (de)	1988-03-24	Weichspuelmittel
EP0688356B1 (fr)	1997-04-23	Compositions aqueuses d'adoucissants textiles
DE4402527A1 (de)	1995-08-03	Wäßrige Lösungen von Esterquats
EP0074078A2 (fr)	1983-03-16	Produit de rinçage adoucissant pour le linge
DE2721847C2 (fr)	1991-04-11
EP0503155B1 (fr)	1996-05-01	Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires
EP0569847A1 (fr)	1993-11-18	Composants non-azotés, utilisés dans les formulations d'adoucissants
EP0835863A1 (fr)	1998-04-15	Esterquats
EP1491617B1 (fr)	2006-09-27	Compositions aqueuses nacrées
DE4400927A1 (de)	1995-07-20	Wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salze
DE19721589A1 (de)	1998-11-26	Textilweichmacherkonzentratre
DE1962919B2 (fr)	1978-06-01
DE3812888A1 (de)	1989-11-02	Textilweichmachende oberflaechenaktive verbindungen